August is nearly over, and summer is hanging by a thread. This pains me. Terribly. Don’t get me wrong – I’m excited for football, crisp autumn days, dark beers, and an abundance of pumpkin-flavored food and beverages. It’s what follows autumn that I abhor.

Anyway, no need to get ahead of ourselves. It’s still summer for a little while, and hopefully we’ll have some pleasant weather as the season shifts. But it’s time to wrap up the Outdoor Seating series while there’s still a month or so to enjoy the simple pleasure of sipping a cocktail in the great urban outdoors. So after a week of drinking on the water, and another hiding out on back decks, we look to the sky for the final installment – rooftop bars.

DSC08263

You’d think more restaurants in Boston would make use of their rooftops. Space is always at a premium here, and relatively few places have enough room for the secluded patios we looked at last time. Roof decks make efficient use of that limited real estate and offer a surprisingly quiet alternative to bars that are often in very congested city areas. Personally, I appreciate the novelty of the experience – the anticipation of walking up a dark staircase and emerging onto a rooftop patio bathed in afternoon sun or illuminated by soft lighting at night, and undetectable from the street. If nothing else, it’s just cool to think “I’m on a roof!”

Our first stop is Harvard Square. Unlike some areas of town that quiet down when school is out of session, Harvard gets even busier in the summer. It feels like a hastily thrown-together collage of shops, restaurants, bars, street musicians, tourists, and a million cars vying for about 20 parking spots.

If the mere thought of dining alfresco amid such constant activity sounds overwhelming, you’ll be surprised to know that there are actually some really good outdoor options in Harvard Square. But if you need to get even further away from the crowds, Daedalus offers a refuge on its roof deck.

Daedalus

DSC08364

Indoors or outdoors, this was my first trip to Daedalus. It’s is a short walk out of Harvard Square proper (sort of on the way to Central), so it’s already a little bit removed from the heaviest foot traffic.

I stopped by at about 6:15 on a Friday evening with Kelly and Ivys, prior to meeting up with the rest of the barhopping crew. At the time I was a little concerned as to whether a roof deck was a good idea; the day had been, by all accounts, a steamah. But the Daedalus roof deck is well equipped to handle even the quirkiest New England summer days, whether it be searing heat or the out-of-nowhere thunderstorms we’ve had all season (not that I think they’d let you out there during a thunderstorm). Large red umbrellas on most of the 15 or so tables keep the sun from baking you, and there’s a covered section with ceiling fans to cool things down.

DSC08267

The roof scene was fairly quiet when we arrived; maybe a dozen people there. By 7 p.m., the whole deck was filling up fast. And despite the scorching heat, the sun was fading and a nice breeze was kicking up.

Since there’s no bar on the Daedalus roof deck, and you must order food in order to drink up there, we grabbed a corner table and began perusing the menu.

Daedalus has a respectable beer list, but if ever there was a time for a cold, fruity cocktail, it was a warm August night like this one. Kelly got things under way with a Caipirinha. Daedalus’s take on the national drink of Brazil was made with Leblon cachaca, fresh limes, and sugar, on the rocks.

DSC08273

I opted for a coconut Mai Tai, which swaps out regular rum for Malibu and throws in a little dark rum for good measure.

DSC08286

After snacking on hummus and pita, we moved onto dinner. Ivys went with the evening’s special – risotto with steak and scallops. It was a delicious combination, kind of like an Italian surf and turf, and was beautifully presented.

DSC08297

Kelly was pleased with her crab cake sandwich, topped with avocado and a spicy chipotle aioli.

DSC08295

I got the Cuban sandwich, which I would characterize as acceptable (and given that the best Cuban money can buy is just a little further up Mass Ave at Chez Henri, I’m being generous).

DSC08301

The Daedalus roof deck is spacious and uncluttered, the wooden tables nicely spread out. Flower beds add color and create the impression of being on a secluded rooftop garden. Cool-looking rectangular lanterns come to life as twilight falls, and the whole deck takes on a peaceful ambience.

DSC08357

Try to hold onto that peaceful feeling when they bring you the check. Daedalus is a lovely environment, no doubt; but the food is seriously overpriced. I’ll give them a pass on the crab cake, which, at $13.95, is comparable to what you’d pay elsewhere. But my Cuban was the same price, and the sandwich was disappointing. Ivys’ risotto was a staggering $21.95. Granted, it was a special, and quite good, but for that price I’d expect more than two steak tips and a few scallops.

Kelly’s Caipirinha (I’ll be glad when I’m done with this section of the post so I can stop looking up how to spell that) was $9, and my coconut Mai Tai was $10. On the one hand, that’s what nicer drinks tend to cost around here; on the other, these weren’t exactly craft cocktails. Pretty good, but nothing special. We’ll call it a draw.

But as I observed in my visits to Alley Bar and RumBa, sometimes you have to pay a little more if you want a certain atmosphere. Prices aside, we had a really nice experience at Daedalus. It’s a beautiful, quiet environment that’s well suited to a summer evening and warrants at least one visit.

DSC08359

While Daedalus creates some secluded rooftop space in busy Harvard Square, the Rattlesnake Bar and Grill does the same thing in Back Bay. Before executive chef Brian Poe put Shangri-La out of its misery and made it the Tip Tap Room, he gave a stunning culinary makeover to the Rattlesnake, a bar that was never exactly renowned for its food. Now it’s a destination, and the highlight is the roof deck.

The Rattlesnake

DSC_0269

The Rattlesnake roof deck is somewhat sparse in terms of its décor, yet it’s also visually striking (kind of like the Tip Tap Room, now that I think of it). While the walls are painted bright red, the bar and the wooden floor are black, providing a nice contrast. The whole area has a nice glow when the lights come on. And if it’s too hot, the Rattlesnake now employs misting machines to keep you cool.

I was here at about 6:30 on a Monday night, and the roof deck was hoppin’. Unlike Daedalus, the Rattlesnake roof deck has its own bar. That made the scene a lot more lively, as it attracts more of an after-work crowd. There are about 15 tables, which were filling up when I got there.

DSC_0277

Rattlesnake offers a handful of cocktails, along with a separate list of margaritas (which was their hallmark before the menu got its upgrade a few years ago). The draft beers on the roof deck are limited – Sam Summer, Harpoon, and Blue Moon, but the bottle and can selection is much more expansive.

I started with a glass of sangria, which has been my warm-weather standby cocktail this year. Refreshing, not too sweet, and perfect for yet another sizzling August evening.

DSC_0280

The advantage of having a bar up here means you can stop in just for drinks, but you’d be foolish to skip the food. The menu is pretty extensive, and as with any Brian Poe creation, very little of it is conventional. Take the corn bread, which I got as an appetizer. As awesomely delicious as corn bread is, it’s a pretty simple, consistent formula. Rattlesnake, by contrast, makes a grilled corn bread and jazzes it up with chiles and Guadalajara butter. The result was rich, dense, and smoky, like Southwestern cuisine colliding with Southern BBQ.

DSC_0284

I probably could have stopped right there, but the undisputed highlight of Rattlesnake’s menu is “Tacos a la Poe,” and I wasn’t skipping that. Forget your typical taco fillings like chicken, beef, or carnitas. Rattlesnake’s tacos are upscale and innovative, and you can choose from fillings such as fish, duck, lamb, and scallops, among others. I got the Spicy Cubano tacos – chipotle- and lime-marinated smoked pork loin, pickles (normally unacceptable on my plate but essential for a Cuban), Swiss cheese, jalapeno pickled red onion, and habanero saffron slaw.

DSC_0294

If I were less vain, I would have taken a picture of my face while I was eating this, since it probably matched the bright red walls. You’d think I’d have learned my lesson after the Toro Furioso episode at Five Horses.

Intense as they were, the tacos were fantastic. Very tender, thinly sliced pork. My mouth aflame, I left the cocktails behind and went for a Blue Moon.

DSC_0287

Prices here are higher than at your typical bar; but then again, this is anything but typical bar food. The corn bread was $8.25, and my tacos were $12.75. Pretty good deal for innovative recipes that you wouldn’t find just anywhere.

The beers are kind of pricey. My Blue Moon was an absurd $6.50 (but after the heat of those tacos, I would have spent $20 for it). The sangria, on the other hand, was $8, which is eminently reasonable.

DSC_0303

For our final destination, we head to one of the most densely packed areas in Boston. The North End crams what feels like 5,000 or so Italian eateries into approximately two city blocks. And summer is probably this neighborhood’s busiest and most popular season; locals and tourists alike hit the North End in full force, clogging its narrow, winding streets, standing in long lines at the pastry shops, and creating interminable waits at many of the small, quaint restaurants. Needless to say, there’s no shortage of options for Italian food here. Yet as far as I know, only Ristorante Fiore has a roof deck – and I can’t think of a better way to escape the chaos.

Ristorante Fiori

DSC09250

And what a roof deck it is. Large and spacious, enclosed by white garden walls and exposed brick, Fiore’s rooftop is comfortable, casual, and impressive. The roof deck has its own bar, with a marble top and a dozen seats. There’s a TV behind the bar and a couple of ceiling fans to keep the air moving on those stifling summer days. The seven tables in the immediate vicinity make for a good apps-and-drinks atmosphere, and there’s a separate dining area with lights strung above it, creating a romantic scene when the sun goes down. A mural painted on the back wall evokes the Italian countryside.

DSC09247

I arrived at 5:30 on a beautiful Monday evening and was surprised to find not another soul at the bar. Both the dining area and the bar started filling up about an hour later, though it never got terribly crowded while I was there.

A summer evening on the roof deck of an Italian restaurant put me in the mood for a glass of white wine. I began with a crisp, refreshing Sauvignon Blanc.

DSC09205

As enjoyable as the wine was, I wished I’d taken a closer look at my surroundings. In front of me was a jug of pineapple-infused vodka. Now that’s not a big deal; plenty of bars infuse their own vodka. Then I noticed a jug of another clear liquid – but with large chunks of coconut. This was unusual. The bartender told me it was coconut-infused rum. What’s more, the two infusions combine to create the Fiore martini, a seasonal specialty that I promptly ordered. Sophisticated tropical perfection.

DSC09230

That seasonal martini is only one option on what is an extensive cocktail list, highlighted by summery selections like a blood orange mojito and a cucumber cooler. And like any Italian restaurant worth its salt, there’s a wine list a mile long.

I wasn’t planning on eating, but I wasn’t planning on ordering a potent martini on top of my wine, either. I got an appetizer of calamari that wasn’t spectacular, but kept me upright.

DSC09238

Fiore’s prices are pretty standard for the North End. My wine was $8, which is reasonable. The cocktails range from $10 to $14, and the calamari was $12. Entrée prices are a little up there, but again, comparable for the area.

What’s incomparable is the experience. There are plenty of restaurants in the North End with huge windows that open onto the street, giving you the comforts of indoor dining with outdoor air and a view of the always bustling Italian neighborhood. But for me, nothing beats a secluded rooftop, far above the crowds, with only the night sky and soft lighting above.

DSC09246

Last Call

As I said when I began this series, finding quality outdoor seating can be a challenge in Boston. Of course, the same could be said for any major city. Gray buildings, loud cars, busy streets, crowded sidewalks – most people don’t relish these sights and sounds when they’re in the mood for a quiet dinner or a few drinks.

In some cases, you might find yourself paying a little more for your relative seclusion; it’s up to you whether the scenery is worth a $7 beer. But there are plenty of places that are affordable and still give you a chance to enjoy the weather.

That said, any bar or restaurant can just stick a few tables and chairs on the sidewalk. But the places that get it right are the ones that find a way to transport you. Whether it’s cocktails by the water, beers on a back deck, or dinner on a rooftop, the best-conceived outdoor seating areas constitute something of a sanctuary – no matter how congested the surrounding area.